diff --git a/ChangeLog.txt b/ChangeLog.txt
index dd7ec248..a705ca97 100644
--- a/ChangeLog.txt
+++ b/ChangeLog.txt
@@ -8,6 +8,7 @@ Broker:
 - Fix bridge not reconnectng if the first reconnection attempt fails.
   Closes #2207.
 - Improve QoS 0 outgoing packet queueing.
+- Fix non-reachable bridge blocking the broker on Windows. Closes #2172.
 
 Clients:
 - If sending mosquitto_sub output to a pipe, mosquitto_sub will now detect
diff --git a/lib/packet_mosq.c b/lib/packet_mosq.c
index d9647182..bce1fe8b 100644
--- a/lib/packet_mosq.c
+++ b/lib/packet_mosq.c
@@ -236,11 +236,7 @@ int packet__write(struct mosquitto *mosq)
 #endif
 
 	state = mosquitto__get_state(mosq);
-#if defined(WITH_TLS) && !defined(WITH_BROKER)
 	if(state == mosq_cs_connect_pending || mosq->want_connect){
-#else
-	if(state == mosq_cs_connect_pending){
-#endif
 		pthread_mutex_unlock(&mosq->current_out_packet_mutex);
 		return MOSQ_ERR_SUCCESS;
 	}
@@ -324,15 +320,17 @@ int packet__write(struct mosquitto *mosq)
 
 #ifdef WITH_BROKER
 		mosq->next_msg_out = db.now_s + mosq->keepalive;
-		if(mosq->current_out_packet == NULL){
-			mux__remove_out(mosq);
-		}
 #else
 		pthread_mutex_lock(&mosq->msgtime_mutex);
 		mosq->next_msg_out = mosquitto_time() + mosq->keepalive;
 		pthread_mutex_unlock(&mosq->msgtime_mutex);
 #endif
 	}
+#ifdef WITH_BROKER
+	if (mosq->current_out_packet == NULL) {
+		mux__remove_out(mosq);
+	}
+#endif
 	pthread_mutex_unlock(&mosq->current_out_packet_mutex);
 	return MOSQ_ERR_SUCCESS;
 }
diff --git a/src/bridge.c b/src/bridge.c
index 3fc0dce8..bb7b9c35 100644
--- a/src/bridge.c
+++ b/src/bridge.c
@@ -285,6 +285,7 @@ int bridge__connect_step2(struct mosquitto *context)
 
 	if(rc == MOSQ_ERR_CONN_PENDING){
 		mosquitto__set_state(context, mosq_cs_connect_pending);
+		mux__add_out(context);
 	}
 	return rc;
 }
@@ -447,6 +448,7 @@ int bridge__connect(struct mosquitto *context)
 		return rc;
 	}else if(rc == MOSQ_ERR_CONN_PENDING){
 		mosquitto__set_state(context, mosq_cs_connect_pending);
+		mux__add_out(context);
 	}
 
 	HASH_ADD(hh_sock, db.contexts_by_sock, sock, sizeof(context->sock), context);